Aldehyde Or Ketone Group In Acid Moiety Patents (Class 560/51)
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Patent number: 5856560Abstract: A process and intermediates for preparing .alpha.Type: GrantFiled: December 10, 1996Date of Patent: January 5, 1999Assignee: BASF AktiengesellschaftInventors: Herbert Bayer, Heinz Isak, Horst Wingert, Hubert Sauter, Michael Keil, Markus Nett, Remy Benoit, Ruth Muller
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Patent number: 5852200Abstract: Cross-coupling or addition reactions of organic compounds, including acid halides, allylic halides, and .alpha.,.beta.-unsaturated carbonyl containing compounds, with organozinc compounds may be readily and safely carried out in the presence of cuprous iodide. The use of this catalyst in the coupling reaction provides for the preparation of commercially useful products in the pharmaceutical, agrochemical and other industries.Type: GrantFiled: August 22, 1996Date of Patent: December 22, 1998Assignee: Rieke Metals, Inc.Inventor: Reuben D. Rieke
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Patent number: 5849793Abstract: There is disclosed a structural genus of compounds, defined according to coordinates in three-dimensional space, that binds amino moieties on neighboring lysine residues in a tyrosine residue 29 pocket of the matrix protein component of the HIV preintegration complex (PIC), thereby preventing the PIC from binding to karyopherin .alpha. and preventing nuclear importation and integration of the HIV viral genome into the host cell DNA, thereby preventing viral infection.Type: GrantFiled: August 15, 1997Date of Patent: December 15, 1998Assignee: The Picower Institute for Medical ResearchInventors: Senliang Pan, Michael Bukrinsky, Omar K. Haffar
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Patent number: 5804595Abstract: The invention provides certain amino acid conjugates of substituted 2-phenyl-N-?1-(phenyl)-2-(1-heterocycloalkyl- or heterocycloaryl-)ethyl!acetamides useful for selectively agonizing kappa opioid receptors in mammalian tissue.Type: GrantFiled: December 5, 1995Date of Patent: September 8, 1998Assignee: Regents of the University of MinnesotaInventors: Philip S. Portoghese, An-Chih Chang
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Patent number: 5801272Abstract: A mixture of (R)- and (S)-2-(4-alkanoylphenoxy)- or (R)- and (S)-2-(4-aroylphenoxy)propionic esters I ##STR1## with an enantiomeric excess of at least 90% is prepared by reacting a mixture of (R) and (S) enantiomer of a 2-phenoxypropionic ester II ##STR2## in which the appropriate (R) or (S) isomer is present in excess, with a carboxylic acid derivative of the formula IIIR.sup.1 --CO--X III,(X=OH, halogen, R.sup.1 COO or sulfonyloxy)in the presence of a Friedel-Crafts catalyst.The (R)- or (S)-2-(4-alkanoylphenoxy)propionic esters and (R)- or (S)-2-(4-hydroxyphenoxy)propionic esters are used for preparing crop protection agents and drugs.Type: GrantFiled: August 11, 1995Date of Patent: September 1, 1998Assignee: BASF AktiengesellschaftInventors: Wolfgang Siegel, Hubert Sauter, Gerhard Schaefer
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Patent number: 5789609Abstract: Disclosed are an optically active diphosphine represented by formula: ##STR1## wherein R represents a lower alkyl group having 1 to 4 carbon atoms; Ar represents a phenyl group which may be substituted with a lower alkyl group having 1 to 4 carbon atoms and/or a lower alkoxy group having 1 to 4 carbon atoms, a transition metal complex containing the diphosphine as a ligand, and a process for producing an optically active .delta.-oxo-.alpha.-cyano ester using the transition metal complex as a catalyst.Type: GrantFiled: October 22, 1997Date of Patent: August 4, 1998Assignee: Takasago International CorporationInventors: Kyoko Tamao, Koji Inagaki, Noboru Sayo
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Patent number: 5776977Abstract: Compounds of formula I, ##STR1## wherein the substituents R.sub.1 -R.sub.4 and a have the given meanings and show an activity against inflammatory conditions.Type: GrantFiled: August 5, 1996Date of Patent: July 7, 1998Assignee: Hoechst AktiengesellschaftInventors: Ramachandra Ganapati Naik, Vilas Narayan Mumbaikar, Rangarajan Vasumathy, Aftab Dawoodbhai Lakdawala, Mandakini Vithalrao Shirole, Bansi Lal, Jurgen Blumbach, Klaus Ulrich Weithmann, Robert Ryder Bartlett
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Patent number: 5739376Abstract: Fullerene derivatives, methods of preparing the same and methods of using the same, wherein the fullerene derivatives are of the formula I ##STR1##Type: GrantFiled: October 20, 1995Date of Patent: April 14, 1998Assignee: Hoechst AktiengesellschaftInventor: Carsten Bingel
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Patent number: 5739374Abstract: Diphenylheteroalkyl derivatives of the formula I ##STR1## where A and R.sup.1 -R.sup.6 have the meanings specified in the description, and the preparation thereof are described.The substances are suitable for controlling diseases and as cosmetic agents.Type: GrantFiled: February 14, 1997Date of Patent: April 14, 1998Assignee: BASF AktiengesellschaftInventors: Bernd Janssen, Hans-Heiner Wuest
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Patent number: 5736274Abstract: A polymer containing a recurring unit of a conjugated N-fluoropyridinium salt and an active material for a positive electrode, an electrolyte, a battery material for the positive electrode and a battery which use such a polymer. That polymer provides a battery material and a primary battery or a secondary battery which have high electromotive force, high energy density, high environmental acceptability, a low internal resistance in charging and discharging and strong recoverability of the electromotive force, and can be useful as a fluorinating agent.Type: GrantFiled: April 18, 1997Date of Patent: April 7, 1998Assignee: Daikin Industries, Ltd.Inventors: Teruo Umemoto, Kenji Adachi, Ginjiro Tomizawa, Sumi Ishihara, Masayuki Nagayoshi
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Patent number: 5716624Abstract: Novel pharmaceutically/cosmetically-active polyaromatic propynyl compounds have the structural formula (1): ##STR1## in which X is one of the radicals: ##STR2## and are useful for the treatment of a wide variety of disease states, whether human or veterinary, for example dermatological, rheumatic, respiratory, cardiovascular and ophthalmological disorders, as well as for the treatment of mammalian skin and hair conditions/disorders.Type: GrantFiled: December 15, 1994Date of Patent: February 10, 1998Assignee: C.I.R.D. GaldermaInventor: Jean-Michel Bernardon
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Patent number: 5703269Abstract: The preparation of aromatic olefins from haloaromatics and olefins (Heck reaction) is carried out in the presence of palladium complexes as catalysts, which complexes contain heterocyclic carbenes as ligands.Type: GrantFiled: December 29, 1995Date of Patent: December 30, 1997Assignee: Hoechst AktiengesellschaftInventors: Wolfgang A. Herrmann, Jakob Fischer, Martina Elison, Christian Kocher
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Patent number: 5688991Abstract: An antioxidant/UV absorbent useful in cosmetics is formed of an ester of ferulic acid with an alkanol having 1 to 12 carbon atoms.Type: GrantFiled: May 8, 1995Date of Patent: November 18, 1997Assignees: Tsuno Food Industrial Co., Ltd., Wakayama PrefectureInventors: Hisaji Taniguchi, Eisaku Nomura, Takuo Tsuno, Seikou Minami
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Patent number: 5681979Abstract: The present invention provides a process for producing alkylcyclopentanone derivatives of formula (1) by reacting alkyl cyclopentanone derivatives of formula (2) and alkyl halides of formula (3) in an organic solvent in the presence of molecular sieves and an alkaline metal hydroxide: ##STR1## wherein R.sup.1 is C.sub.1 -C.sub.4 alkyl group; R.sup.2 is hydrogen atom or C.sub.1 -C.sub.5 alkyl group; R.sup.3 is C.sub.1 -C.sub.5 alkyl group; Y is halogen atom, C.sub.1 -C.sub.5 alkyl group, C.sub.1 -C.sub.5 haloalkyl group, phenyl group, cyano group or nitro group; n is an integer from 0 to 5; when n is 2 or greater, Y's may be identical or different; R.sup.3 in formula (3) is the same as R.sup.3 in formula (1); and a process for preparing alkylcyclopentanone derivatives of formula (5) by reacting cyclopentanone derivatives of formula (4) and alkyl halides of formula (6) in an organic solvent in the presence of molecular sieves and an alkaline metal hydroxide: ##STR2## wherein R.sup.1 is C.sub.1 -C.sub.Type: GrantFiled: March 1, 1996Date of Patent: October 28, 1997Assignee: Kureha Kagaku Kogyo Kabushiki KaishaInventors: Hajime Hoshi, Satoru Kumazawa
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Patent number: 5663412Abstract: The present invention relates to substantially pure piperidine derivative compounds of the formulae: ##STR1## wherein R.sub.1 is hydrogen or hydroxy;R.sub.2 is hydrogen;or R.sub.1 and R.sub.2 taken together form a second bond between the carbon atoms bearing R.sub.1 and R.sub.2 ;R.sub.3 is --COOH or --COOR.sub.4 ;R.sub.4 has 1 to 6 carbon atoms;A, B, and D are the substituents of their respective rings each of which may be different or the same and are hydrogen, halogens, alkyl, hydroxy, alkoxy, or other substituents.A process of preparing such piperidine derivative compounds in substantially pure form is also disclosed.Type: GrantFiled: August 8, 1996Date of Patent: September 2, 1997Assignee: Albany Molecular Research, Inc.Inventor: Thomas E. D'Ambra
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Patent number: 5656619Abstract: Abstract of the Disclosure: Diphenylheteroalkyl derivatives of the formula I ##STR1## where A and R.sup.1 -R.sup.6 have the meanings specified in the description, and the preparation thereof are described.The substances are suitable for controlling diseases and as cosmetic agents.Type: GrantFiled: June 6, 1995Date of Patent: August 12, 1997Assignee: BASF AktiengesellschaftInventors: Bernd Janssen, Hans-Heiner Wuest
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Patent number: 5587505Abstract: Triterpene derivatives of the formula (I): ##STR1## wherein R.sup.1 is hydrogen or metabolic ester residue; and R.sup.2 is hydrogen or --R.sup.3 -R.sup.4 wherein R.sup.3 is --SO.sub.3 --, --CH.sub.2 COO--, --COCOO--, or --COR.sup.5 COO-- (R.sup.5 is lower alkylene or lower alkenylene), and R.sup.4 is hydrogen or metabolic ester residue or a pharmaceutically acceptable salt thereof, which have anti-endothelin activities and are useful in prophylaxis and treatment of diseases caused by excessive secretion of endothelin.Type: GrantFiled: July 26, 1995Date of Patent: December 24, 1996Assignee: Shionogi & Co., Ltd.Inventors: Toshiro Konoike, Yoshitaka Araki, Tetsuyoshi Hayashi, Kensuke Sakurai, Takehiko Tozyo
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Patent number: 5569778Abstract: A process for preparing a fluorine-containing dicarbonyl compound of the formula: R.sup.1 COCFR.sup.2 COR.sup.3 in which R.sup.1 is a hydrogen atom, or a substituted or unsubstituted alkyl or aryl group; R.sup.2 is a hydrogen atom, a halogen atom, or a substituted or unsubstituted alkyl or aryl group; and R.sup.3 is a hydrogen atom, or a substituted or unsubstituted alkyl, aryl, alkoxy or aryloxy group, provided that at least two of R.sup.1, R.sup.2 and R.sup.3 may together form a part of a cyclic structure with or without a hetero atom, by reacting a dicarbonyl compound of the formula: R.sup.1 COCHR.sup.2 COR.sup.3 in which R.sup.1, R.sup.2 and R.sup.3 are the same as defined above with fluorine (F.sub.2) in at least one solvent selected from the group consisting of halogenated hydrocarbons having 1 to 5 carbon atoms and nitrile compounds, or in a solvent in the presence of a salt, or an acid having pKa of 6 or less.Type: GrantFiled: April 28, 1995Date of Patent: October 29, 1996Assignee: Daikin Industries Ltd.Inventors: Teruo Umemoto, Ginjiro Tomizawa
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Patent number: 5536874Abstract: There is provided a process for preparing an arylacetic acid or arylpropionic acid divative from an arylcarbinol which comprises the step of subjecting said arylcarbinol to suitable carbonylation conditions for a sufficient period of time and under suitable pressure and temperature to form said acid derivative, with the proviso that said carbonylation conditions include conducting the reaction in a two-phase system wherein one phase is an aqueous medium which contains (1) a catalyst which is a water-soluble metal complex consisting essentially of a Group VIII metal and a hydrophilic ligand such as palladium complexed with trisulfonated triphenylphosphine, and (2) optionally an acid, and wherein the second phase comprises said arylcarbinol.Type: GrantFiled: November 30, 1994Date of Patent: July 16, 1996Assignee: Hoechst Celanese CorporationInventors: Roger A. Sheldon, Leendert Maat, Georgios Papadogianakis
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Patent number: 5523459Abstract: A process for preparing an .alpha.-keto acid ester (oxo acid) of the formula: ##STR1## wherein R.sup.1 is a hydrogen atom, aliphatic alkyl group of 1-6 carbon atoms, phenyl group or benzyl group, and R.sup.2 is an aliphatic alkyl group of 1-6 carbon atoms, which comprises causing an .alpha.-hydroxycarboxylic acid ester of the formula: ##STR2## to react with molecular oxygen in a gaseous phase in the presence of copper phosphate, possibly, mounted on a solid carrier.Type: GrantFiled: March 27, 1995Date of Patent: June 4, 1996Assignee: Ube Industries, Ltd.Inventors: Koichi Hirai, Yasuo Nakamura, Kiyotaka Yoshii, Yasunori Fukuda
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Patent number: 5519160Abstract: Derivatives of alkyl 3-(substituted or unsubstituted benzylidene)-1-alkyl-2-oxocylopentanecarboxylate of the following formula (I), ##STR1## wherein R.sup.1 and R.sup.2 individually represent a lower alkyl group; X is a halogen atom, a cyano group, an alkyl group, a haloalkyl group, a phenyl group, or a nitro group; and m is an integer of 0 to 5; provided when m is 2 or larger, Xs may be either the same or different. The compounds are useful themselves as an effective ingredient of antifungal compositions, and can be used for intermediates of agriculture chemicals and medicines.Type: GrantFiled: November 15, 1994Date of Patent: May 21, 1996Assignee: Kureha Chemical Industry Co., Ltd.Inventors: Heitaro Obara, Satoru Kumazawa
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Patent number: 5516931Abstract: A release tag reagent suitable for use in the chemical analysis of a substance to be detected comprises signal, release, and reactivity groups. A class of release tag compounds that are cleaved to release as signal groups very stable electrophoric ketones which are sufficiently volatile for determination in the gas phase of an analytical reaction mixture is disclosed.Type: GrantFiled: April 22, 1993Date of Patent: May 14, 1996Assignee: Northeastern UniversityInventors: Roger W. Giese, Samy Abdel-Baky, Linxiao Xu
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Patent number: 5475132Abstract: R.sub.3, R.sub.4 and R.sub.5, each represents a hydrogen or halogen atom (at least one of R.sub.3, R.sub.4 and R.sub.5 being other than hydrogen or halogen); optionally substituted amino; optionally halogenated or hydroxylated alkyl, alkoxy, alkylalkoxy or alkylthio; or R.sub.3 and R.sub.4 (in the 3- and 4-positions) can together form a single divalent radical with 3 or 4 members containing 1 or 2 non-adjacent oxygen atoms; are useful as agricultural fungicides.Type: GrantFiled: May 27, 1994Date of Patent: December 12, 1995Assignee: Rhone-Poulenc AgrochimieInventors: Regis Pepin, Christian Schmitz, Guy-Bernard Lacroix, Philippe Dellis, Christine Veyrat
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Patent number: 5473071Abstract: Pyrido[2,3-d]pyrimidine compounds are prepared through the reaction of 2,4-diamino-6(1H)-pyrimidone and an activated derivative of a dialdehyde. A typical embodiment utilizes the dinitrile.Type: GrantFiled: November 6, 1989Date of Patent: December 5, 1995Assignee: Trustees of Princeton UniversityInventors: Edward C. Taylor, Philip M. Harrington
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Patent number: 5466880Abstract: A novel multi-step process for preparing the (4S)-enantiomer of 4-(3,4 -dichlorophenyl)-3,4-1(2H)- naphthalenone in a highly-optically pure form is disclosed. The process involved starts from the known 4-(3,4-dichlorophenyl)-4-ketobutanoic acid and proceeds through such intermediates as (1) isopropyl or tert.- butyl 4-(3,4 -dichlorophenyl)-4-ketobutanoate, (2) isopropyl or tert.-butyl 4-(3,4-dichlorophenyl)-(4R)-hydroxybutanoate, (3) isopropyl or tert.-butyl 4-(3,4-dichlorophenyl-(4R)-sulfonyloxybutanoate, (4) isopropyl or tert.-butyl 4-(3,4-dichlorophenyl)-(4R)-phenylbutanoate to finally yield the desired (4S)-4-(3,4-dichlorophenyl)-3,4-dihydro -1(2H)-naphthalenone compound in a highly-optically pure form. The latter compound, which is a (4S)-enantiomer per se, has utility as an intermediate that ultimately leads to pure cis-(1S)(4S)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthal eneamine (sertraline), which is a known antidepressant agent. The aforementioned isopropyl and tert.Type: GrantFiled: June 9, 1994Date of Patent: November 14, 1995Assignee: Pfizer Inc.Inventor: George J. Quallich
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Patent number: 5446158Abstract: A process is described for the total synthesis of the macrolide immunosuppressant, FK-506, and important tricarbonyl process intermediates thereof. The tricarbonyl intermediates can be produced by the mild oxidation of 2,3-dihydroxy carboxylate compounds containing olefin moieties.Type: GrantFiled: October 12, 1990Date of Patent: August 29, 1995Assignee: Merck & Co., Inc.Inventors: Todd K. Jones, Sander G. Mills, David Askin, Robert A. Reamer, Richard Desmond, David M. Tschaen, Ralph P. Volante, Ichiro Shinkai
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Patent number: 5436369Abstract: Certain novel alicyclic compounds are effective phospholipase A.sub.2 (PLA.sub.2) inhibitors.Type: GrantFiled: February 23, 1994Date of Patent: July 25, 1995Assignee: Bristol-Myers Squibb CompanyInventors: Joanne J. Bronson, Katharine M. Greene, Muzammil M. Mansuri, Stanley V. D'Andrea, F. Ivy Carroll, Anita Lewin
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Patent number: 5434186Abstract: Compounds of the formula ##STR1## wherein X is O or CH.sub.2 ; Y is O, --CH.sub.2 --CH.sub.2 --, --CH.dbd.CH--, --C.tbd.C--, or --OCH.sub.2 C.sub.6 H.sub.4 --;Z is --CH.sub.2 --CH.sub.2 --, --CH.dbd.CH-- or --C.tbd.C--;f, h, k, m and t, independently, are 0 or 1;n is an integer from 1 to 12;R.sup.1 is hydrogen, lower alkyl, lower alkenyl, cycloalkyl, or aralkyl; and A is B or --O--B, wherein B is a mono-, di- or tricyclic aromatic or heteroaromatic moiety substituted by the group --COR.sup.2, --(O).sub.t --(W).sub.s --COR.sup.2 or --(CH.dbd.CH).sub.p COR.sup.2 and which may also contain up to 4 additional substituents selected, independently, from the group consisting of halogen, cyano, lower alkyl, lower alkoxy, sulfonamido, alkanoyl, aroyl, --(Q).sub.k --(W).sub.s' --E or --(Q).sub.k --(W).sub.s" --C.sub.6 H.sub.4 --(W).sub.s'" --E, provided that no more than one of said substituents is --(Q).sub.k --(W).sub.s' --E or --(Q).sub.k --(W).sub.s" --C.sub.6 H.sub.4 --(W).sub.s'" --E, and wherein E is COR.sup.Type: GrantFiled: September 28, 1993Date of Patent: July 18, 1995Assignee: Hoffmann-La Roche Inc.Inventors: Noal Cohen, Ferdinand K. Lee, Keith A. Yagaloff
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Patent number: 5434292Abstract: A novel phenylalkanoic acid derivative represented by the following formula ##STR1## wherein n is an integer of 1-2, X is a halogen atom, alkoxyl group or nitro group, R is a hydrogen atom or alkyl group, and Z is a hydrogen atom or acyl group,a method for producing said derivative, a method for separating the optical isomers of said derivative from each other, as well as an anti-inflammatory drug, analgesic drug or preparation for external use each containing said derivative.Type: GrantFiled: February 4, 1994Date of Patent: July 18, 1995Assignee: Hisamitsu Pharmaceutical Co., Inc.Inventors: Masaru Saita, Hisataka Inoue, Koichi Beppu, Terumi Hachiya, Ikuo Shinohara, Yasuaki Taniguchi, Yoshiki Deguchi, Yoshihiro Hamaguchi
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Patent number: 5430172Abstract: A process for preparing 4-alkanoylaryl benzyl ethers of the general formula I ##STR1## where R is hydrogen, halogen, cyano; alkyl, alkoxy;X is CH.sub.2, CH--CH.sub.3, CH--CH.sub.2 --CH.sub.3, CH--OCH.sub.3 or N--OCH.sub.3 ;Y is oxygen, sulfur, direct linkage or nitrogen;m is 0, 1, 2 or 3;R.sup.1 is hydrogen; alkyl, alkenyl, alkynyl or alkoxy;R.sup.2 is cyano, halogen, alkyl, alkoxy or haloalkyl;R.sup.3 is alkyl; haloalkyl; cycloalkyl; or an unsubstituted or substituted mono- to trinuclear aromatic system,comprises reacting an aryl benzyl ether of the general formula II ##STR2## where X, Y, R, R.sup.1, R.sup.2 and m have the abovementioned meanings, with a carbonyl halide or with a carboxylic anhydride or with a carboxylic sulfonic anhydride in the presence of an acid and in the presence or absence of a diluent.Type: GrantFiled: April 15, 1994Date of Patent: July 4, 1995Assignee: BASF AktiengesellschaftInventors: Wassilios Grammenos, Wolfgang Siegel, Klaus Oberdorf, Bernd Mueller, Hubert Sauter, Reinhard Doetzer
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Patent number: 5420340Abstract: A compound of the formula ##STR1## wherein Ar is phenyl optionally substituted with at least one member of the group consisting of halogen, methylenedioxy, phenyl, phenoxy, --CF.sub.3 and alkyl, alkoxy and alkylthio of 1 to 6 carbon atoms, Z is selected from the group consisting of hydrogen, chlorine, --CF.sub.3 and alkyl, alkoxy and alkylthio of 1 to 6 carbon atoms, R.sub.1 and R.sub.2 are individually alkyl of 1 to 6 carbon atoms and the exocyclic double bonds independently have (E) or (Z) geometry having fungicidal activity and a process for their preparation.Type: GrantFiled: January 12, 1994Date of Patent: May 30, 1995Assignee: Roussel UclafInventors: Jean-Louis Brayer, Jean-Pierre Demoute, Gilles Mourioux
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Patent number: 5416211Abstract: Processes for preparing 5-substituted pyrrolo[2,3-d]pyrimidines which are useful as intermediates for the preparation of pyrrolo[2,3-d]pyrimidine antineoplastic agents or as antineoplastic agents themselves are provided.Type: GrantFiled: May 24, 1993Date of Patent: May 16, 1995Assignee: Eli Lilly and CompanyInventors: Charles J. Barnett, Thomas M. Wilson
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Patent number: 5414105Abstract: Disclosed herein are an azole derivative represented by the formula (I): ##STR1## wherein R.sup.1 and R.sup.2 respectively represent a (C.sub.1 -C.sub.5) alkyl group or a hydrogen atom; X represents a halogen atom, a (C.sub.1-C.sub.5) alkyl group or a phenyl group; n represents an integer of from 0 to 2 and A represents a nitrogen atom or a CH, provided that R.sup.1 is not a hydrogen atom when R.sup.2 is a hydrogen atom, a process for producing the azole derivative represented by the formula (I), and an agricultural and horticultural composition containing the azole derivative represented by the formula (I).Type: GrantFiled: May 17, 1993Date of Patent: May 9, 1995Assignee: Kureha Kagaku Kogyo Kabushiki KaishaInventors: Satoru Kumazawa, Susumu Shimizu, Hiroyuki Enari, Atsushi Ito, Susumu Ikeda, Nobuo Sato, Toshihide Saishoji
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Patent number: 5403952Abstract: Novel substituted cyclic compounds of Formula I are found to be useful inhibitors of matrix metalloendoproteinase-mediated diseases including osteoarthritis, rheumatoid arthritis, septic arthritis, tumor invasion in certain cancers, periodontal disease, corneal ulceration, proteinuria, dystrophic epidermolysis bullosa, and coronary thrombosis associated with atherosclerotic plaque rupture. The matrix metalloendoproteinases are a family of zinc-containing proteinases including but not limited to stromelysin, collagenase, and gelatinase, that are capable of degrading the major components of articular cartilage and basement membranes. The inhibitors claimed herein may also be useful in preventing the pathological sequelae following a traumatic injury that could lead to a permanent disability. These compounds may also be useful as novel birth control agents by preventing ovulation or implantation.Type: GrantFiled: October 8, 1993Date of Patent: April 4, 1995Assignee: Merck & Co., Inc.Inventors: William Hagmann, Charles G. Caldwell, Paul R. Gooley
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Patent number: 5399747Abstract: A new process for preparing aryl-substituted aliphatic carboxylic acids is provided. Aryl-substituted aliphatic ether or thioether compound is reacted with carbon monoxide in aqueous conditions at a temperature between about 25.degree. C. and about 200.degree. C. An acid such as hydrochloric acid may be added. As catalyst, a mixture of palladium or a palladium compound and a copper compound with at least one acid-stable ligand are present.Type: GrantFiled: January 27, 1994Date of Patent: March 21, 1995Assignee: Albemarle CorporationInventors: Kannappan Chockalingam, Tse-Chong Wu
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Patent number: 5391817Abstract: Certain novel biaryl compounds are effective phospholipase A.sub.2 (PLA.sub.2) inhibitors.Type: GrantFiled: December 21, 1993Date of Patent: February 21, 1995Assignee: Bristol-Myers SquibbInventors: Dane Springer, Bing-Yu Luh, Katharine M. Greene, Joanne J. Bronson, Muzammil M. Mansuri
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Patent number: 5391811Abstract: .alpha.-fluoro-.beta.-dicarbonyl compounds are prepared by reacting a halogenated dicarbonyl compound at temperatures of 20.degree. to 100.degree. C. with an addition product of hydrogen fluoride and a trialkylamine. This process is easy to carry out in technical terms and can also be carried out on a large scale.Type: GrantFiled: November 3, 1993Date of Patent: February 21, 1995Assignee: Bayer AktiengesellschaftInventors: Stefan Bohm, Albrecht Marhold
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Patent number: 5385902Abstract: Antimicrobial compounds of the formula ##STR1## wherein A is selected from the group consisting of alkyl; phenyl; alkoxy; phenoxy; benzyloxy; monoalkylamino; dialkylamino; cyclic amino, anilino; heterocyclic; amino substituted with heterocyclic ring, methods of making and using said compounds, and compositions comprising said compounds are disclosed.Type: GrantFiled: September 1, 1993Date of Patent: January 31, 1995Assignee: Rohm and Haas CompanyInventor: Adam C. Hsu
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Patent number: 5380718Abstract: Arthropodicidal tetrahydropyridazines of Formulae I and II, ##STR1## wherein Q,X,X.sup.1 Y, and G are as defined in the text, compositions containing them and their use in the control of arthropods.Type: GrantFiled: November 12, 1992Date of Patent: January 10, 1995Assignee: E. I. Du Pont de Nemours and CompanyInventors: Charles R. Harrison, George P. Lahm, Thomas M. Stevenson
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Patent number: 5380860Abstract: A method for preparing a compound of the formula ##STR1## wherein Q is C--H or N; R.sup.1 is C.sub.1-C.sub.4 alkyl, benzyl or p-nitrobenzyl and X and Y are independently selected from fluoro and chloro comprising reacting a compound of the formula ##STR2## wherein Q is >C--H or N; X and Y are independently selected from fluoro and chloro; and Z is fluoro, chloro, 1-imidazolyl or substituted 1-imidazolyl, wherein the 1-imidazolyl group is substituted with one or two substituents independently selected from C.sub.1 to C.sub.4 alkyl, with a compound of the formula[M.sup.n+ ].sub.p [V.sup.p- ].sub.nwherein M is an alkaline earth metal, Cu or Mn, n is 2, V.sup.p-, wherein p is 1 or 2, is an anion of the formula ##STR3## or a dianion of the formula ##STR4## and R.sup.1 is C.sub.1 to C.sub.6 alkyl or paranitrobenzyl, with the proviso that when Z is 1-imidazolyl or substituted 1-imidazole, M is magnesium, copper or manganese and with the proviso that when Z is fluoro, chloro or bromo, V.sup.Type: GrantFiled: January 24, 1992Date of Patent: January 10, 1995Assignee: Pfizer Inc.Inventors: Frank R. Busch, Richard S. Lehner, Brian T. O'Neill
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Patent number: 5378728Abstract: Compound of the formula ##STR1## where R is CH.sub.3 (CH.sub.2).sub.m, A and B are hydrogen, a bond or --(CH.sub.2).sub.n,X is ##STR2## m is 0, 1 , 2 or 3, n is 1 , 2, or 3, R.sub.1 is hydrogen or lower alkyl, andY is --OH, --OR.sub.2 or --NR.sub.3 R.sub.4where R.sub.2, R.sub.3 and R.sub.4 are hydrogen or unsubstituted or substituted alkyl, aryl and aralkyl substituents.Type: GrantFiled: September 20, 1993Date of Patent: January 3, 1995Assignee: Sandoz Ltd.Inventors: Jeffrey Nadelson, William R. J. Simpson, Robert C. Anderson, Joginder S. Bajwa
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Patent number: 5360924Abstract: Process for preparing aromatic olefins of the formula (1) ##STR1## in which R.sup.1 -R.sup.3 are hydrogen, alkyl (C.sub.1 -C.sub.8) , alkoxy-(C.sub.1 -C.sub.5), phenyl, fluorine, chlorine, bromine, --OH, --NO.sub.2, --CN, --CHO, --COalkyl(C.sub.1 -C.sub.4) , --COphenyl, --COOalkyl (C.sub.1 -C.sub.4) , --OCOalkyl(C.sub.1 -C.sub.4), --NHCOalkyl(C.sub.1 -C.sub.4) , --CF.sub.3, --NH.sub.2, --NH--alkyl(C.sub.1 -C.sub.4) or --N(alkyl(C.sub.1 -C.sub.4)).sub.2 and R.sup.4 is hydrogen, alkyl(C.sub.1 -C.sub.8), phenyl, fluorine, chlorine, bromine, --OH, --NO.sub.2, --CN, --CHO or --OCOalkyl (C.sub.1 -C.sub.4) , and X is, inter alia, alkenyl(C.sub.2 -C.sub.12) or cycloalkenyl(C.sub.4 -C.sub.8) or the group ##STR2## in which R.sup.5 and R.sup.6 are, independently of one another, hydrogen or methyl, and Y is --phenyl, --CN, --COOH, --COOalkyl(C.sub.1 -C.sub.12), --COOphenyl, ##STR3## --CON (phenyl).sub.2, --COalkyl(C.sub.1 -C.sub.12), --COphenyl, --Oalkyl(C.sub.1 -C.sub.12) , --Ophenyl or the radical ##STR4## in which R.Type: GrantFiled: January 6, 1994Date of Patent: November 1, 1994Assignee: Hoechst AktiengesellschaftInventors: Matthias Beller, Hartmut Fischer, Heinz Strutz
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Patent number: 5359126Abstract: Preparing cyclohexanediones of the formula ##STR1## an aldehyde is reacted with a ketene to give a polymer having the repeating unit ##STR2## wherein n ranges from about 2 to about 1,000. The polymer is hydrolyzed to produce a mixture of an unsaturated acid of the formula R--CH.dbd.C(R.sub.1)--COOH and a hydroxy ester or acid of the formula R--CH(OH)C(R.sub.1)(R.sub.2)--COOR.sub.3, the mixture is then contacted with an esterifying agent to convert the acids to esters. The ester mixture is contacted with a dehydrating agent to convert the hydroxy ester to unsaturated ester of the formula R--CH.dbd.C(R.sub.1)--COOR.sub.3. The unsaturated ester is contacted with a basic catalyst to cyclize it to the cyclic dione ester of the formula ##STR3## and this ester is then hydrolyzed and decarboxylated to give the cyclohexanedione give the productwherein:R is selected, e.g.Type: GrantFiled: February 7, 1994Date of Patent: October 25, 1994Assignee: Eastman Chemical CompanyInventor: Charles A. McCombs
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Patent number: 5356919Abstract: This invention relates to a compound of the formula: ##STR1## or a pharmaceutically acceptable salt thereof wherein X is oxygen, sulfur, --CH.dbd.CH--, or --CH.dbd.N--; wherein R.sup.1 is --CO.sub.2 R.sup.2 or tetrazole; wherein R.sup.2 is hydrogen, alkyl of 1 to 6 carbons or a pharmaceutically acceptable cation; wherein R is an alkyl of from 1 to 20 carbons, --(CH.sub.2).sub.p CF.sub.3 or --(CH.sub.2).sub.q R.sup.3 wherein R.sup.3 is alkoxy, phenoxy or alkoxy substituted phenoxy wherein the alkoxy group has from 1 to 8 carbons; wherein p and q are integers from 0 to 20; wherein n is 0 or 1; and wherein m is 0, 1, 2, or 3.Type: GrantFiled: May 30, 1991Date of Patent: October 18, 1994Assignee: G. D. Searle & Co.Inventors: Stevan W. Djuric, Richard A. Haack, Julie M. Miyashiro
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Patent number: 5352820Abstract: The invention is an expedient route to synthesizing substituted or unsubstituted aryl-2-propenoic esters. The substituted or unsubstituted aryl-2-propenoic esters are useful in preparing optically active substituted or unsubstituted 2-arylpropanoic acids known to be active anti-inflammatory agents.Type: GrantFiled: June 28, 1993Date of Patent: October 4, 1994Inventor: Jeremy I. Levin
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Patent number: 5344959Abstract: Compounds of the formula ##STR1## wherein m is 1-4; R.sub.1 -R.sub.4 independently are hydrogen, lower alkyl of 1 to 6 carbons, Cl, Br, or I; R.sub.5 is hydrogen, lower alkyl of 1 to 6 carbons, Cl, Br, I, lower alkoxy or lower thioalkoxy of 1-6 carbons; R.sub.6 is hydrogen, lower alkyl, Cl, Br, I, OR.sub.11, SR.sub.11, OCOR.sub.11, SCOR.sub.11, NH2, NHR.sub.11, N(R.sub.11).sub.2, NHCOR.sub.11 OR NR.sub.11 --COR.sub.11 ; R.sub.20 is independently hydrogen or lower alkyl; A is (CH.sub.2).sub.n where n is 0-5, lower branched chain alkyl having 3-6 carbons, cycloalkyl having 3-6 carbons, alkenyl having 2-6 carbons and 1 or 2 double bonds, alkynyl having 2-6 carbons and 1 or 2 triple bonds; B is hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR.sub.8, CONR.sub.9 R.sub.10, --CH.sub.2 OH, CH.sub.2 OR.sub.11, CH.sub.2 OCOR.sub.11, CHO, CH(OR.sub.12).sub.2, CHOR.sub.13 O, --COR.sub.7, CR.sub.7 (OR.sub.12).sub.2, or CR.sub.7 OR.sub.13 O, where R.sub.Type: GrantFiled: May 18, 1993Date of Patent: September 6, 1994Assignee: Allergan, Inc.Inventor: Roshantha A. Chandraratna
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Patent number: 5344939Abstract: The preparation of magnesium benzyl fluoromalonate and other equivalent materials, the synthetic equivalents of the --CH.sub.2 F moiety, is described. Reaction between these reagents and the in situ-formed imidazolides of various carboxylic acids gives beta-keto-alpha-fluoroesters, which upon hydrogenation and spontaneous decarboxylation yields fluoromethyl ketones in excellent yields. The overall transformation from RCOOH to RCOCH.sub.2 F is thus illustrated.Type: GrantFiled: March 11, 1993Date of Patent: September 6, 1994Assignee: Prototek, Inc.Inventor: James T. Palmer
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Patent number: 5326900Abstract: Compounds of the general formula I ##STR1## and drugs and cosmetics prepared therefrom are described.Type: GrantFiled: December 4, 1992Date of Patent: July 5, 1994Assignee: BASF AktiengesellschaftInventors: Hans-Heiner Wuest, Bernd Janssen
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Patent number: 5319123Abstract: N-oxy substituted imidic acid derivative of the formula ##STR1## where R.sub.1, R.sub.2 and R.sub.3 are alkyl and aryl substituents, which are useful as antidiabetic and hypolipidemic agents are prepared by the following procedure: ##STR2## where X is chlorine, bromine, or iodine, and R.sub.1 ' is the same as R.sub.1 but with any hydroxy or carboxy groups present protected by a hydroxy or carboxy protecting group and, when R.sub.1 ' is a protected hydroxy or carboxy substituent, deprotecting the substituent.Type: GrantFiled: May 17, 1991Date of Patent: June 7, 1994Assignee: Sandoz Ltd.Inventors: George T. Lee, Ustun B. Sunay, Prasad K. Kapa
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Patent number: H1705Abstract: A process for the preparation of 2-carboalkoxy-1-indanones of Formula I from 1-indanones of Formula II using a dialkyl carbonate and an alkali metal alkoxide is provided. This process is superior to the prior art in that it avoids pyrophoric reagents such as sodium hydride, and proceeds in high chemical yield and product quality. The invention provides a novel process to an important intermediate in the preparation of arthropodicidal carboxanilides of commercial interest. ##STR1## wherein: R.sup.1, R.sup.2 and M are defined in the specification.Type: GrantFiled: April 28, 1997Date of Patent: January 6, 1998Assignee: E. I. du Pont de Nemours and CompanyInventors: Donald Joseph Dumas, William Christopher Hollinsed